Aunt Mary's Dress Shoppe Pt. 01

Not even one full semester and I was flunking out of college. I knew this was gonna happen. I was never good in school and barely maintained a "C" average. I hated sports too. No reason to think I would do well at college but my parents had insisted.

They had money and even though I could only get into a state school, they were proud.

Until they saw my grades that is.

Dad had told me that if I didn't graduate that I couldn't come home or work in his business doing landscaping and grounds management. Not that I had any interest in that anyway but not being allowed to come home was hurtful, even for my mom whom was quite a bit more sympathetic.

So I started calling around to relatives looking for a place to crash. All my cousins told me no and so did my uncle on my father's side but my aunt on my mother's side said I could rent a room in her house and even pick up some paid work sweeping floors in her shoppe.

I waited around college for a couple weeks to see if my grades would improve and I really did try but to no avail so I accepted Aunt Mary's invitation. At least I would have a place to live and a little bit of money coming in till I could find a decent job.

I took a Greyhound bus out to my aunt's place with the full weight of failure hanging on me.

"Hello Cammy." my aunt said giving me a great big hug. I hated that nickname. My aunt always added a "Y" to the end of everyone's name so Jo became Joey, Mike became Mikey and Cameron became Cammy. Ugh. Double ugh.

"Hi, Aunt Mary, thanks for letting me crash. Dads all in a twist about me flunking out of college and wont let me stay at home." I said as I tossed my bags in the trunk of her Cadillac.

"Your father is an asshole, always was. I warned your mother about him many times but she only saw his bank account. Now she's paying the price in a loveless marriage. Remember this Cammy dear, happiness is always better than money." my aunt said. She had an annoying habit of talking forever. "Oh and by the way. I haven't cleared out everything from your room yet, I hope you dont mind. I wasn't sure you were coming after all."

"Yeah, I stayed at school and I did try it's just not for me" I explained.

"Well like I said, happiness is far more important than money so if college wasn't making you happy then find another path. Maybe coming here is the start of a whole new life for you. By the way, I'm expanding my workshop and I have plenty of work for a few months the help you get on your feet." she said.

She kept talking about family, her dress shoppe, what was for dinner, what mom was like as a kid. It went on and on and on. She did like to talk.

We got back to her house, a grand place in town with more space than she would ever need and I was shown to what would become my room. Right now it was used for storage and was full of sewing mannequins. There were at least thirty of them standing all over and more than a few boxes piled up as well. There was a bed but it was piled high with dresses that looked as if they had been there for a few years.

"I'm so sorry about the mess. I'll tell you what. Since you're gonna be working for me, why don't you start by cleaning out this room for me. It'll probably be enough work to give you a full paycheck to start with. Plus the room will be the way you like it. Huh, what do you think?" she offered

Get paid to clean my own room? It was a huge room too and anyone would be glad to have it.

"Hell yeah. I can do that but where do I put all this stuff?" I said.

"Right then. You can put everything you don't need in the store room plus you'll be cleaning that out too. Like I said, I've got a ton of work for you. It'll be nice to have someone around to talk to. I can never keep anyone on staff." She said sighing.

I took a little time to get to know the place and realized that fully half the house was set up as Aunt Mary's dress shoppe and there was plenty of space left over. Must be nice to work at home. Of coarse, technically now I'm working from home.

I started by hauling mannequins down to the store room one at a time as I managed to make space for them. The first four were fairly normal ladies mannequins in various states of dress. But the fifth was obviously a male mannequin and it had on a bra and panties as well as high heels.

Confused by the last mannequin, I went to Aunt Mary to ask about it.

"Aunt Mary, I have a question. Why are their male mannequins dressed in girly stuff?" I asked as my aunt was busy altering some sort of dress for a client.

"Oh, I make a lot of dresses for men these days. I have several sewing forms for men around here somewhere. By the way, that's what they are called, sewing forms, not mannequins. Anyway, I do a lot of business online and there a lot of men who enjoy the finer things in life. Remember what I told you about happiness Cammy." she explained.

Well, that was a bit weird but not really. When I was at college there were school sponsored drag queen events so why not?

I decided to refrain from dragging anymore sewing forms, as Aunt Mary called them, down to the store room and just concentrate on clearing off the bed so I would have a place to sleep tonight.

What a frilly nightmare. Panties, skirts, dresses, slips, bras, stockings and every manner of girly frills. I actually got hard boxing some of the stuff up and that made me think of the male sewing forms and the people who bought those dresses.

I looked around and it didn't take long to see a male sewing form that was probably my size and it had on a short skirted maids dress that did little to hide the panties it was wearing. Frilly things covered with rows and rows of lace.

I went back to cleaning off the bed getting ever more excited as I did.

Finally when it was cleaned off and all the girly things were in boxes, I decided to take a break. It was well after noon when I had arrived and a good deal later now and I was hungry.

Aunt Mary had made sandwiches for dinner and as I ate them all I could think about was the sewing form with the maids dress and frilly panties.

"Do you mind if I knock off early today Aunt Mary. Riding on that bus was tiring and I'd just rather be done with today and hit the sack? I asked wondering if I could have some alone time with those pretty and frilly things all over my new room.

"Absolutely, you must be exhausted. Get some rest and start up again after breakfast tomorrow."She said.

I quickly went up to my bedroom and after making sure my aunt went back to her business, I carefully stripped the maids dress off the sewing form. It was more than a dress and came with a flared out underskirt which is what made the panties visible.

I stripped naked and put the outfit on. My dick got hard as a rock immediately. The shoes were just a tad too big for me but I still wore them just out of curiosity. There was no mirror in my room so I had no real idea what I looked like but I did wonder about men who liked to wear a dress.

Were all crossdressers gay? I didn't know but I suspected that many were. I looked around the room for another male sewing form and found one by the door wearing only a bra along with stockings and a garter belt. This sewing form was bigger than I was, in fact many of the ladies sewing forms were bigger than I was. I wasn't a particularly big person, rather the opposite.

The sewing form wasn't anatomically correct or anything like that but I did wonder what that must be like. I knelt down in my borrowed maids dress and tentatively placed my face where the cock should have been and gently stuck out my tongue and licked it right in the crotch.

And the door swung open and my aunt walked in carrying an armful of linens for the bed.

"I was just... Um... I mean... It's not what... I'm sorry." I stammered embarrassed as I quickly got to my feet only to trip in the heels and land on my ass with skirt up and panties exposed.

"I'm so sorry, I was just playing around." I said continuing to plead.

"You don't need to apologize or be embarrassed. Remember what I told you about happiness. Do what makes you happy and you'll never regret it." she said as I struggled to my feet then added, "I just thought I would bring some clean sheets for the bed."

I took the pile of folded sheets and noted right away they were made of silk and said, "Um, thank you Aunt Mary."

"You do look pretty in that getup. Maybe I'll have some work for you if you'd be interested in modeling a dress from time to time. Go ahead and get your bed made up and I'll be back in minute. And never be afraid to be who you are dear." she said leaving me alone but with the door open.

My heart hadn't beat in nearly a minute I was so scared.

I kicked off the heels before I made my way through the assorted clutter back to my bed so I didn't accidentally fall again but kept the dress on while I made up my bed as I thought it would be worse if Aunt Mary came in while I was changing or even naked.

I was halfway through making the bed when she returned and I was glad I hadn't decided to change yet. She would have caught me naked for sure.

"Here you go. I have four for you to choose from and a little surprise for your friend over by the door." she said as she handed me several nightgowns. She then left.

Holy shit, here for less than one day and busted playing dressup. I sat on the bed to calm myself. Well at least she was okay with it although I would never be able to look her in the eyes again.

I finished making the bed and decided to take off the maids dress but kept the panties on and then pulled one of the nightgowns, a pink one that was very short, over my head.

I looked at the small box that was a little larger than a shoebox which contained whatever Aunt Mary said was for my 'friend' by the door referring to the sewing form whose crotch I had licked.

I opened it and inside was a leather harness with an attached silicon cock. I recognized it as a strapon.

I guess she really was okay with it. I had never even considered doing anything remotely gay or in a dress and here I was about to...

I went back the the sewing form and with a little difficulty fastened the strapon onto it. I then knelt down again and gingerly kissed it before taking it in my mouth. I felt so submissive and somehow it felt good. It felt right.

I wondered what it would feel like in my ass when I heard... Knock, knock.

I stopped sucking and hurried back to my bed and got under the silk sheets before yelling, "Come in."

She came in and I saw her eyes go to the sewing form with the strapon right away.

"Would you like to talk?" she asked, how long have you been hiding this?"

"Well, actually this was the first time I ever put on a anything girly. I was just curious and the whole room was full of stuff making me excited." I explained.

"I see. Did you like wearing a dress then?" she asked.

"Yeah, I guess." I answered.

"And tell me, did you enjoy the toy for the dress form?" she inquired further.

"My jaw got sore after a few minutes." I said.

"Lots of girls complain about that but in truth it's not a big deal as most men finish way to quickly for your jaw to get sore. Did you wonder what it would be like to have it in your bottom?" she asked almost like she was talking to her own daughter.

"I guess, maybe." I answered honestly.

"Okay then, I'll be back in a few minutes and show you." she said and left again leaving the door open.

When she returned she carefully sat at the foot of my bed and said, "Okay young lady, off with the covers and lift your gown for me."

I pulled the sheet off revealing the short nightgown I had chosen to wear. She then gently pulled my legs apart. I thought she was gonna stick a butt plug or a dildo in me but instead she lifted her skirts revealing a strapon of her own with the cock pointed down. She turned it halfway and now it was erect.

It was smaller than the one she gave me to suck on, long but very skinny, and she placed it at my ass.

She lubed me up with a single finger and then entered me with the silicon dong. It was so skinny that it hardly hurt but my dick was once again hard as a rock. I moaned loudly as my violation proceeded.

"Now just remember, when your wearing a dress, that's not a penis anymore, it's a clitoris and your bottom is a pussy. Now say it for me?" she said as she began to move in out out of me in a fucking motion.

I grabbed my dick and said, this is my clitoris and your fucking my pussy.

I stroked myself about four times before I shot my load all over the nightgown and some of it got into Aunt Mary's skirts as well.